Lindsay Lohan Ch. 01

Story Info
Lindsay Lohan & Older Man.
7.5k words
4.33
41k
25

Part 1 of the 3 part series

Updated 09/22/2022
Created 05/07/2012
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Author's Note: The following story is a work of pure fiction. It is meant purely as erotic fun and offence is intended to anyone. Particulary Lindsay Lohan who I remain a big fan of.

Earl Saunders had been a judge for over 20 years and for the most part he had enjoyed his time with the gavel. He had presided over many hundreds of cases sometimes giving people a fair chance and when deserved punishing people to the full extent of the law. About a year ago Earl had turned 60 and had started to feel like maybe it was time to think about retirement. In truth his passion for the job had started to dwindle and his enthusiasm was at an all time low.

It did not help that the current case in his court room with both difficult and annoying. It should have been a simple case of broken probation which Earl would usually have pushed through before quickly without too much deliberation. But that was never going to happen with this case because of the celebrity factor. Earl hated celebrities and he hated all the publicity and aggravation that seemed to follow when a celebrity came into his court room.

In truth Earl himself had never heard of the defendant. His notes told him the basic facts. Her name was Lindsay Dee Lohan, she was 25 years old and that apparently she was quite a famous actress. Today Miss Lohan had arrived in his court 35 minutes late claiming the press and crowds outside were to blame. Earl who hated tardiness had not been impressed but was forced to accept her excuse because in truth there were undoubtedly many people outside causing much chaos and confusion.

Lindsay Dee Lohan was accused of breaking her probation several times. She had been caught out later then her curfew allowed and she had been caught drinking even though she had been told to stop for the duration of her probation. For the last hour her lawyer had been making a case excusing her of all the charges while Miss Lohan had sat there quietly behind big black sunglasses. In his younger days Earl would have made her remove the sunglasses in his court but he could not be bothered now. As far as Earl was concerned the sooner this case ended the better.

Personally Earl did not think that Miss Lohan was a bad person. She was young and famous and had made a few mistakes sure but she was not like the many murderers or rapists Earl had had before him over the years. This case was in Earl's opinion a waste of time and money.

"Your honour?" Earl suddenly realised he had been lost in thought and not realised that the lawyer had finished making his point. "Thank you for that Mr Johnson." Earl quickly said trying to act as though he had been listening all along. "It was a most intelligent and well argued case. I will now retire to my chambers and make my decision. Court is dismissed for lunch. Miss Lohan I will ask you to remain inside the walls of this courtroom for lunch so that you are not late returning. My decision will not take long." Earl stood and headed for his chambers.

About an hour later Earl was sat in his chair behind his desk. It had taken him about 5 minutes to decide he was going to cut Miss Lohan some slack and let her off with a warning but it would never do to return after 5 minutes. He had to make it look like he had thought long and hard about this decision. The only thing that worried Earl was that Miss Lohan clearly needed somebody to tell her some home truths. Miss Lohan had already served a small amount of time in prison and all these petty charges were quickly adding up to a much longer sentence. Sure Earl was going to let her get away with it this time but next time there would be no second chances.

In Earl's opinion Miss Lohan needed somebody to talk straight to her and explain to her the trouble she was headed for. Could he get through to her? If he called her into his private chambers now could he talk some sense into her? Could he maybe scare her enough to change her ways? Earl decided to give it a go. What the heck it was worth a try.

15 minutes later there was a knock at the door of his chambers and in walked Miss Lohan and her lawyer. "Mr Johnson I asked to speak to Miss Lohan alone you are not needed right now." Earl explained.

"But your honour if you wish to speak to my client then I should be present." said the lawyer.

"Mr Johnson I assure that Miss Lohan will not need your services during this meeting and I am not requesting that you leave, I am telling you to." Earl said this sternly leaving the lawyer no doubt that he would lose this argument.

The lawyer looked annoyed but followed his instructions and left the room closing the door a bit harder then was necessary but at least he was gone. "That's better," said Earl "Now Miss Lohan please take a seat and let us have a chat about your future."

Lindsay Lohan sat in the chair opposite and Earl. This was the first time Earl had seen Miss Lohan up close. Earl's eyes were not as good as they used to be and she had sat too far away to get a good look in the courtroom.

Earl was quite surprised by the beauty of this young girl. Her blonde hair reminded him of his boyhood crush Marilyn Monroe. She still wore the sunglasses but beneath them were a beautiful and full pair of red lips. She was wearing a red dress completely inappropriate for a courtroom. The dress was short and ended about midway down her thighs. When she sat she crossed her legs and the dress rode an inch higher.

Earl spent the next 15 minutes explaining things as he saw them. All the while Miss Lohan sat behind those glasses looking almost bored. At no time did she say anything or make any attempt to act like she was interested in what Earl was saying.

"Miss Lohan am I boring you?" asked Earl.

The girl looked like she was going to ignore Earl's question at first but then answered in a voice sounding a little older then her 25 years. "Your honour this is all so totally boring and I don't understand why I have to stay here all day."

"Miss Lohan this is your future we are talking about after all."

"Your honour I understand that, but couldn't you talk about these things with my lawyer or maybe my mom? I just don't understand why it has to be me who has to spend all day listening to this stuff. It's not like I don't have better things to be doing."

Earl began to grow annoyed. He was trying his best to help this girl and she clearly had no interest in listening. Earl decided to change tactics and try to scare this spoiled Hollywood brat into taking an interest.

"Miss Lohan do you have better things to be doing for the next 5 years? Because that's how long I am going to sentence you. How does 5 years in jail sound to you Miss Lohan?"

The threat had the desired effect. The entire colour drained from the face of the young girl and she suddenly sat bolt upright in her chair. "Your honour that's crazy I can't go to jail for 5 years. I would be 30 when I got out and that's really old for a Hollywood actress like me."

"Miss Lohan I care not for your acting career." said Earl "You need to learn that there consequences for your actions and the law applies to celebrities as well as normal people. I'll tell you what Miss Lohan I will give you 30 minutes to explain to me why I shouldn't sentence you to 5 years in jail. This is your chance to plead your case."

"Your honour......I......I'm not a lawyer" the clearly distressed starlet pleaded. "How can I be expected to do this?"

"Well Miss Lohan you can start by taking off those ridiculous sunglasses and then you can tell me about your life, your problems and your hopes for the future should you avoid jail."

Lindsay Lohan removed her glasses and began to plead her case. It was story Earl had heard many times before. Father didn't love her. Mother pushed her too hard as a young child. Earl sat back into his chair and continued to listen. The girl looked genuinely worried and finally she was making an effort. To be fair to her she was also making a pretty good case and Earl guessed that she must be quite a good actor.

She also had beautiful eyes and Earl found himself wondering why she hid them behind sunglasses all the time. Earl was 61 years old and he began to wonder if he had ever had a woman as beautiful as this in his courtroom before?

She was small probably no more than 5 and half foot tall. She had the most amazing skin which was almost pale except for the freckles which seemed to run down her entire body. Despite her small frame she seemed to have a quite impressive bust. In fact on closer inspection Earl could see that her tiny dress was in fact struggling to contain that bust and there was quite an amazing cleavage on show. Earl wasn't sure but it looked like Miss Lohan wasn't wearing a bra.

All of a sudden Earl found himself uncomfortable in his chair. It had been quite a few years but Earl found himself trying to conceal an erection in his pants. He felt like a teenage boy rather than the sixty something Judge he was.

As the young actress continued her story Earl found himself thinking about what it would be like to fuck this beautiful Hollywood actress. He knew it was a crazy idea but still he couldn't help but think about it and his prick swelled inside his pants so much that it was becoming sore.

When he was a younger man Earl had been somewhat of a womaniser. He had definitely had his fair share of women before he met his wife but in the 35 years of marriage he had shared with her he had never once strayed from the marital bed.

And yet here he was with a raging erection for another woman. Earl tried to remember the last time he and his wife made love but it had been too long, at least a year thought Earl, maybe even two? Earl didn't get aroused much anymore. He was too old and too out of shape for that sort of thing.

But not today. Today just looking at this young woman had made him harder than he had been in years. If he was 30 years younger Earl believed he would have definitely made a move on this delicious creature. But not now, not now that he was so old. There was no way a woman like this would ever go for a man as old as Earl. Not unless she was a freak who found wrinkles, thinning grey hair and a pot belly attractive.

But then Earl had a thought. He doesn't have to seduce this young actress. Why should he even bother trying? After all it was Earl who had all the power. It was Earl who could send this Lindsay Dee Lohan to jail if she didn't give him what he wanted. Earl wondered what would happen if he just bluntly gave her the option to either fuck him or face 5 years in jail?

Earl suddenly realised that the girl had stopped talking. "Your honour are you like even listening to me anymore?" she asked. Earl looked at her and wished he was 30 years younger. Wow she really was beautiful.

"Miss Lohan do you have a boyfriend?" he asked.

"Er......You see I'm not really like into guys all that much." she replied.

"How do you mean?" asked Earl "Too busy with your career for boys?"

"Well not exactly your honour......you see I kinda like girls." Replied Lindsay.

This shocked Earl who never imagined such a beautiful girl would be gay. "So your a lesbian Miss Lohan?" he asked.

"OMG your honour!" replied the girl "I'm not totally sure that's any of your business but I think maybe I am. At least I could be. My last relationship was with a woman anyway."

"And has there ever been any men in your life Miss Lohan?"

"I had boyfriends when I was younger I guess but not for awhile now." replied the actress.

Earl could see that the girl was getting uncomfortable with these questions and Earl knew that he had no right asking them. The smart thing to do now would be to change the subject and end this meeting as quickly as possible but Earl wasn't thinking as clearly as he normally did. Right now his rock hard cock was thinking for him.

Earl surprised himself by asking "Miss Lohan when did you last have sex with a man?" Earl knew this was the key moment. The question was completely inappropriate and she would either get up and storm out or she would....."About 4 years ago I guess." she answered pleasantly surprising Earl.

There was no doubt about it, Earl knew he had gone over the line with his questioning but so far the girl had not reacted badly. In fact she seemed to answer his questions quite willingly. But could he possibly push it any further? Maybe he should quit while he was ahead.

"Miss Lohan you seem quite a smart young woman and I fail to see why you continually allow yourself to get into trouble." Earl had lost his nerve and decided to backtrack on his recent line of questioning. "Miss Lohan do you think if I gave you one more chance that you would take it and behave yourself this time?"

"Oh yes your honour I would totally do things differently this time. I promise. I just need you to give me a chance to prove it."

Earl decided that he quite liked this young girl and he would give her that chance to change her life around. He already knew a jail sentence was out of the question and now he figured the best thing was just to let the girl go completely and hope she never mentions to her lawyer Earl's inappropriate questions concerning her sex life.

"Do I have to suck your cock?"

The question came out of nowhere and shocked Earl into his seat. Had he misheard the girl? Surely he had. "Excuse me Miss Lohan? What did you just say?" he asked.

"Sorry your honour," she apologised "I meant your penis, do I have to suck your penis?"

"Miss Lohan.....I er...." Earl stammered to think of what to say next.

The actress cut him off "For the chance I mean? Do I have to perform er.....fellatio on you? Is that the correct term? Fellatio?"

Earl almost felt sorry for the girl; she was clearly trying to use words to impress him. He considered his options here. He should dismiss the girl, put all this behind him and go home to his wife. But here was this beautiful young girl offering him oral sex and Earl felt like he couldn't pass that up even if it did mean cheating on his wife.

"Miss Lohan are you offering to perform oral sex on me if I give you that one last chance?"

Lindsay Lohan sat in her chair and for a minute it looked to Earl as if she was changing her mind on the offer but then in a sincere voice she answered him "Yes your honour."

"Miss Lohan what makes you think I would want that?" Earl asked.

"Well........I thought a couple of times you were like undressing me with your eyes and then you asked about my sex life and I'm pretty sure you already have a massive boner.....er sorry I mean erection. And your like a man and don't all men want that sort of thing?"

"And your prepared to do that Miss Lohan?"

"Your honour I just really don't want to go to jail." she replied "I'll do it if you promise not to send me to jail." The girl stopped and seemed to think of something and then quickly continued "But I do have some rules."

"Ok Miss Lohan what are your rules?" Earl asked.

"Ok so you keep me out of jail and I'll like perform oral sex on you but that's it. I mean I'm not getting naked and I'm definitely not going to have proper sex with you." She stopped thought for a second and continued "And you cant ever tell anyone about this. I have enough problems with my reputation in the press without this ever getting out."

Earl could not believe his luck. Not only did she want to do this but she was actually worried about it being leaked to the press. Earl knew that whatever happened in this room today would stay in this room. He could get oral sex from this young celebrity and his reputation and marriage would remain intact.

Earl sat stunned in his chair unsure how to proceed. He knew that he wanted it to happen but he couldn't bring himself to ask her for it. The two of them sat in silence for a what seemed like ages but was probably only a couple of minutes.

"Do you want me to start now your Honour?" Lindsay asked breaking the silence.

Earl thought about everything. His reputation. His pride. His morals. His marriage. But only one word left his mouth................"Yes".

Lindsay slowly got up out of her chair and stood for a moment in front of Earl. She straightened her dress and then looked across to the room towards him. Earl was once again struck by the beauty of this young woman and he felt guilty even though he had at no point suggested or even agreed to the deal. She began to slowly walk around his desk and the heels of her shoes clacking against the floor were the only sound in the room.

Earl turned his chair so that he could meet her face on. She stood for a moment directly in front of him and Earl had to look up to meet her eyes but before he could say anything she quickly dropped to her knees in front of him.

Earl felt his stomach in his mouth and his heart was beating faster than it had in years. She reached out with one arm and Earl felt her hand touch the hard lump in his pants. Earl grew instantly harder and his cock strained to be released from its confines.

She stopped and looked up to meet his eyes again. "Nobody will come in here right?" she asked "I mean your door isn't locked or anything."

Earl could barely speak but managed to reply in a quiet and shaken voice "I assure you Miss Lohan that nobody would dare enter my chambers uninvited."

This seemed to be all the assurance that the girl needed because immediately Earl heard the zipper on his pants being pulled down. Next she used both hands to undo his belt and the button above the zipper.

"Stand up." she said and Earl rose from his chair. His legs feeling weak and his head almost spinning.

Standing on shaky legs the kneeling girl reached up, grasped hold of his pants and tugged. They immediately fell to the floor around his ankles. Then she immediately raised her hands again and this time hooked a thumb into each side of his underwear. Earl's heart seemed to stop as she quickly pulled his underwear down and his throbbing cock was freed to spring into the air.

Earl stood in front of the girl, his pants and underwear around his ankles and his rock solid cock exposed and slightly twitching in the air. For a moment he felt embarrassed and then he felt a soft hand grasp hold of his cock and begin to rub it gently. The hand made smooth deliberate strokes up and down the length of his cock.

The strokes continued their slow deliberate pace and Earl craned his neck and looked directly up at the ceiling of his chambers letting out a soft moan.

He was just blindly staring at his ceiling when suddenly he felt the unmistakeable feeling of warm breath and then a soft wet flick of a tongue to the tip of his cock. A second later Earl experienced himself entering her soft wet mouth.

Earl continued looking at the ceiling as if looking down would break this amazing feeling. The mouth around his cock started to move up and down his length. Earl could feel the tongue on the underside while on top there was a pleasurable sharpness of teeth.

The mouth started to increase speed and Earl felt his cock being fully enveloped and then almost released but then fully enveloped again. Over and over again he felt this sensation. The girl clearly knew what she was doing and Earl began to worry that all this would be over in a moment because he was close to cumming.

Earl suddenly realised he was still looking at the ceiling. He slowly forced himself to look down and there sure enough he saw the famous young actress on her knees in front of him with his now wet cock sliding in and out of her mouth.

Earl also noticed that she was not using her hands to help with the oral sex choosing instead just to move her head forward and backwards while sucking hard on his length. She was also really starting to pick up speed and the motion was more than Earl could handle. He felt as though his balls were ready to explode and he knew that in a moment he would cum inside her mouth.